Radical Cation Diels-Alder Cycloadditions by Visible Light Photocatalysis

被引:331
作者
Lin, Shishi [1 ]
Ischay, Michael A. [1 ]
Fry, Charles G. [1 ]
Yoon, Tehshik P. [1 ]
机构
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
关键词
PHOTOREDOX CATALYSIS; SELECTIVITY; INDOLE; PHOTOCHEMISTRY; PHOTOPHYSICS; MECHANISMS; COMPLEXES;
D O I
10.1021/ja2093579
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ruthenium(II) polypyridyl complexes promote the efficient radical cation Diels-Alder cycloaddition of electron-rich dienophiles upon irradiation with visible light. These reactions enable facile [4 + 2] cycloadditions that would be electronically mismatched under thermal conditions. Key to the success of this methodology is the availability of ligand-modified ruthenium complexes that enable rational tuning of the electrochemical properties of the catalyst without significantly perturbing the overall photophysical properties of the system.
引用
收藏
页码:19350 / 19353
页数:4
相关论文
共 46 条
[1]   Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7274-7276
[2]   THEORY OF CATION-RADICAL PERICYCLIC-REACTIONS [J].
BAULD, NL ;
BELLVILLE, DJ ;
PABON, R ;
CHELSKY, R ;
GREEN, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2378-2382
[3]   Stereospecificity and mechanism in cation radical Diels-Alder and cyclobutanation reactions [J].
Bauld, NL ;
Yang, JK .
ORGANIC LETTERS, 1999, 1 (05) :773-774
[4]  
Bear BR, 2001, ANGEW CHEM INT EDIT, V40, P821
[5]   THEORETICAL-ANALYSIS OF SELECTIVITY IN THE CATION-RADICAL DIELS-ALDER [J].
BELLVILLE, DJ ;
BAULD, NL ;
PABON, R ;
GARDNER, SA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) :3584-3588
[6]   THE CATION-RADICAL CATALYZED DIELS-ALDER REACTION [J].
BELLVILLE, DJ ;
WIRTH, DD ;
BAULD, NL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) :718-720
[7]   RADICAL CATION AND TRIPLEX DIELS-ALDER REACTIONS OF 1,3-CYCLOHEXADIENE [J].
CALHOUN, GC ;
SCHUSTER, GB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (22) :6870-6871
[8]   A biomolecule-compatible visible-light-induced azide reduction from a DNA-encoded reaction-discovery system [J].
Chen, Yiyun ;
Kamlet, Adam S. ;
Steinman, Jonathan B. ;
Liu, David R. .
NATURE CHEMISTRY, 2011, 3 (02) :146-153
[9]   PHOTOCHEMICAL 2+2 CYCLOADDITION VIA A CATION-RADICAL CHAIN REACTION [J].
CRELLIN, RA ;
LAMBERT, MC ;
LEDWITH, A .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (11) :682-&
[10]   RUTHENIUM(II) TRIS(BIPYRAZYL) DICATION - A NEW PHOTOCATALYST [J].
CRUTCHLEY, RJ ;
LEVER, ABP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (23) :7128-7129